My Tokyo Happy Ending Massage Changed Everything I Thought I Knew About Sex and Pleasure

There was a full moon outside the hotel window, my best friend was downstairs in the lobby, and a strange man was jerking me off with a vibrator. No, this wasn’t a fantasy; this was my real life. We didn’t go to Tokyo with the intention of being sex tourists, but that's what happened.

Thirty minutes earlier, I’d rushed up the elevator and through the hall to meet my erotic masseuse. As I approached our hotel room door, I was greeted by a twenty-something Japanese man with flawless skin holding a gift bag.

We exchanged hellos in each other’s language and then, giggling, went inside. I was buzzing at an 11, a little drunk and electric with anticipation coursing through my body. My nervous energy bubbled over as I fumbled with the key card.

So how did I get here, on the verge of my first happy ending massage?

We expected her to answer with maybe a sightseeing recommendation or some whacky anime dessert. But Hiroko said, “The one thing I want you guys to try is a male prostitute.” (Ahem, to clarify: By “prostitute,” she was referring to erotic masseuses that did not engage in “insertion” and instead performed services like kissing, licking, and fingering—in case you were looking for a more ~technical~ definition.) She’d interviewed one of the top erotic masseuses for work and seemed to suggest that she had been tempted to experiment with the experience but never did. I think she was excited about having us be the guinea pigs.

We laughed initially, though you can hear on the tape that we were quickly intrigued by the suggestion.

Earlier in the interview, Hiroko described the levels of sex and intimacy work in Japan, from faux boyfriend or girlfriend-stye companionship available at host/hostess clubs up to Soaplands, which are the closest thing to American- style brothels. Hiroko explained that one level below Soaplands is a service called “delivery health,” which is basically like Postmates for ladies who want to get off. She told us thousands of guys auditioned to work at one of the “delivery health” agencies, like American Idol for gigolos. Those accepted were specially trained with fingering techniques that titillate women without penetration. (Yes, Tokyo is truly a magical place.)

What’s funny is that when Hiroko first told us about the service, I’d pictured older women clientele in my mind. I didn't see myself as a potential consumer. But when she suggested we try it, it felt like a dare in the best way possible.

I’m in a monogamous, long-term relationship—now he’s my fiancé, but he was my live-in boyfriend at the time—so I needed permission. I felt emboldened by my plausible excuse: I was in Tokyo to do research for my sex podcast, after all! I didn’t want to pay for a long-distance call, plus I wanted to give him time to think about it, so I sent him a text: Hey baby! Someone we interviewed recommended we get an erotic massage (no sex obvs!) but I just wanted to ask you if that’s cool with you first. Lmk 😘.

Nervous and excited, butterflies danced in my stomach while I waited for a response. But I didn’t have to wait long. Four minutes later, he replied: Lol yeah no prob 😘.

My jaw dropped. What an awesome response! Strangely, it made me want to marry him. My boyfriend had always seemed like he would be a good husband, but this was a defining moment that seriously reinforced his life-partner potential.

My co-host and I went to a Denny’s-like Japanese restaurant with Hiroko, where she ordered our masseuses for later that night. Mine had a crown next to his name on the website, indicating he was a top provider, and I couldn’t wait to find out what that felt like in practice. As we dined, we discussed our “pre- game” plans, which found us bar-hopping around Shinjuku and eventually landing at an S&M club in Ginza (as one does), where we completely lost track of time thanks to some very attentive hostesses who never let our glasses run empty. I guess time flies when you’re pre-gaming your erotic massage.

We got a cab and rushed back to our hotel. I scampered up the elevator and through the hall to meet my erotic masseuse. The anticipation was wild!

Once we got to the bed in my hotel room, I just stood there in silence for a second. I’d never done this before, so I tried to ask how the whole thing worked. But beyond saying hi, we didn’t have many words in common. Awkward giggles ensued as I got out my phone and opened Google Translate to tap out: “I’ve never done this before. You show me what to do.”

He took over from there, ushering me to the shower—as it’s apparently customary for both parties to shower beforehand (and sometimes after too). While he took his turn, I found out the unassuming gift bag had been loaded with an arsenal of sex toys that were now carefully placed on the bed alongside a bottle of massage oil and a bottle of lube.

After his shower, it was finally time for the main event. He oiled me up as I laid face-down on the bed, gave me a very short massage with oil, then moved on to the erotic portion. I recognized some of the expert fingering, butterfly kissing, and sucking techniques that Hiroko had mentioned. Then he moved on to the vibrators, cycling through a few different options from his bag of tricks. My masseuse had a boner, which I took as a compliment. But, ever the professional, he kept the focus on me. It was thrilling just to have a stranger’s hands on my body. I felt like I was living a fantasy.

I didn’t cum during the actual massage. Ironically, I was too excited. Instead, I felt a sexy euphoria that started with my masseuse’s first touch and lasted well after I landed back in Los Angeles and resumed my regular life. It was like edging for a full week—well worth the 11,000 yen (AKA just over $100 at the time).

Usually, my best friend and I inevitably wind up fighting at the end of our travels together. But this trip was different—there’s no room for negativity after a happy ending! The next day, we were literally skipping through Tokyo on the way to the airport. We were beside ourselves, barely able to believe our good fortune, exclaiming: How great was that?! I’ve never felt like my pleasure was such a priority!

Would I recommend a friend get a happy-ending massage? A million times, yes. We were joking that we might start leading tours to Tokyo so more women could give it a try.

It was an experience that changed me on multiple levels. To have my sexual satisfaction taken so seriously—literally like it was a job—felt very empowering as a woman. That’s not how our culture is typically oriented. We take for granted that men are desirous and deserving of pleasure, but we don’t tend to let women have that same sexual purchasing power. And oh my God, what a HUGE turn-on!

It was a different kind of release than I get from a typical romantic exchange, and it expanded my mind to aspects of open relationships I hadn’t considered before. I was blown away by how cool my boyfriend was about allowing me to have this experience inside our up-until-now monogamous relationship. It helped me realize that dalliances like this can lend a little extra spice to an LTR without going full poly.

I was so horny on the airplane home, cramped in my economy seat on an international flight, that I tried to watch porn on my phone covertly. It was a threesome scenario: a couple hiring a lady sex worker in Amsterdam. I straddled a ridge in the seat and rocked myself into it hard. A couple of Chinese schoolboys across the aisle burst out laughing. They were onto me, clowning on me and pointing me out to their friends, but not even that could stop my grinding. I was so turned on.

It was obvious that what happens in Tokyo doesn’t necessarily stay in Tokyo—that extra erotic euphoria was a persistent stowaway. As soon as my boyfriend picked me up from the airport in LA, I mauled him with kisses. I couldn’t stop touching him in the car and when we got home, I could hardly wait to rip his clothes off and fuck. We’re both busy, and we’d gotten in a little rut of not prioritizing sex before the trip, but my happy ending reinvigorated us both.

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